EP1990847B1 - Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials - Google Patents

Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials Download PDF

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Publication number
EP1990847B1
EP1990847B1 EP07009366.1A EP07009366A EP1990847B1 EP 1990847 B1 EP1990847 B1 EP 1990847B1 EP 07009366 A EP07009366 A EP 07009366A EP 1990847 B1 EP1990847 B1 EP 1990847B1
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Prior art keywords
dopant
organic
substituted
derivatives
bisimidazoles
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German (de)
English (en)
French (fr)
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EP1990847A1 (de
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Horst Hartmann
Olaf Zeika
Martin Ammann
Rene Dathe
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NovaLED GmbH
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NovaLED GmbH
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Priority to EP07009366.1A priority Critical patent/EP1990847B1/de
Priority to TW97117323A priority patent/TWI471403B/zh
Priority to PCT/EP2008/003792 priority patent/WO2008138580A1/de
Priority to US12/599,487 priority patent/US8460581B2/en
Priority to JP2010506863A priority patent/JP2010530845A/ja
Publication of EP1990847A1 publication Critical patent/EP1990847A1/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to the use of quinoid bisimidazoles and their derivatives as p- dopant for doping an organic semiconducting matrix material in electronic or optoelectronic components.
  • Inorganic dopants such as Lewis acids as electron acceptors (eg FeCl 3, SbCl 5 ), are generally disadvantageous in organic matrix materials due to their high diffusion coefficients, since they impair the function and stability of the electronic components ( D. Oeter, Ch. Ziegler, W. Göpel Synthetic Metals 1993, 61, 147-50 ; Y. Yamamoto, S. Kanda, S. Kusabayashi, T. Nogaito, K. Ito, H. Mikawa, Bull. Chem. Soc. Jap. 1968, 38, 2015-17 ; J. Kido et al. Jpn J. Appl. Phys. 2002, 41, 358-60 ).
  • Lewis acids eg FeCl 3, SbCl 5
  • the latter dopants have such a high vapor pressure that a technical use in known processing systems for organic-electronic components is very questionable.
  • the reduction potentials of these compounds are often too low to dope technically interesting matrix materials.
  • the extremely aggressive chemical reaction behavior of these dopants makes a technical application more difficult.
  • quinoid bisimidazoles are known for use as a charge injection layer or as a matrix material, but in which the imidazole units are linked by a bridge.
  • JP 63-172274 describes the use of various organic compounds in photoconductive films in electrophotography.
  • a film used in electrophotography can not be doped at all because the charged surface could not hold the charge and therefore the image in this case due to the increased conductivity.
  • the quinoid bisimidazoles used should have sufficiently high reduction potentials, without interfering with the matrix material, and provide an effective increase in charge carrier diversity in the matrix material and be relatively easy to handle, in terms of their use in the processing of electronic components.
  • the first object is achieved by the use of quinoid bisimidazoles and derivatives thereof as p-dopant for doping an organic semiconductive matrix material in electronic or optoelectronic components, wherein the quinoid bisimidazoles are represented by the following formula: wherein each Y is independently selected from the group consisting of hydrogen, substituted and unsubstituted arylene, substituted and unsubstituted heteroarylene, substituted and unsubstituted conjugated hydrocarbon chains having alternating C-C single and double bonds, halogen, cyano, pseudo-halogen, nitro , Fluoro and perfluoroalkylene, carboxylic acid and its derivatives, sulfonic acids and their derivatives, or wherein two adjacent Y are part of an aromatic ring system fused to the imidazole ring.
  • Arylene and heteroarylene are also understood as meaning oligo- and polyaryls or heteroaryls.
  • aromatic ring system fused to the imidazole ring is substituted.
  • the invention likewise provides an organic semiconductive material containing at least one organic matrix compound and a p-dopant, wherein at least one compound of the following formula is used as the p-dopant: wherein each Y is independently selected from the group consisting of hydrogen, substituted and unsubstituted arylene, substituted and unsubstituted heteroarylene, substituted and unsubstituted conjugated hydrocarbon chains having alternating C-C single and double bonds, halogen, cyano, pseudo-halogen, nitro , Fluoro and perfluoroalkylene, carboxylic acid and its derivatives, sulfonic acids and their derivatives, or wherein two adjacent Y are part of an aromatic ring system fused to the imidazole ring.
  • the molar doping ratio of dopant to matrix molecule or the doping ratio of dopant to monomeric units of a polymeric matrix molecule is between 20: 1 and 1: 100,000, preferably 10: 1 and 1: 1000, particularly preferably 1: 1 and 1: 100, is.
  • an electronic or optoelectronic device having an electronically functionally effective region, wherein the electronically functionally effective region comprises an organic semiconductive matrix material, which with at least one p-dopant for changing the electronic properties of the semiconductive matrix material using at least one compound of the following formula is doped: wherein each Y is independently selected from the group consisting of hydrogen, substituted and unsubstituted arylene, substituted and unsubstituted heteroarylene, substituted and unsubstituted conjugated hydrocarbon chains having alternating C-C single and double bonds, halogen, cyano, pseudohalogen, nitro, fluoro and perfluoroalkylene, Carboxylic acid and its derivatives, sulfonic acids and derivatives thereof, or wherein two adjacent Y are part of an aromatic ring system fused to the imidazole ring and optionally the aromatic ring system fused to the imidazole ring is substituted.
  • the electronic or optoelectronic component is in the form of an organic light-emitting diode, a photovoltaic cell, an organic solar cell, an organic diode or an organic field-effect transistor.
  • the invention also provides for the use of the quinoid bisimidazoles having the above structural formula as a p-dopant for doping an organic semiconductive matrix material in a p-doped layer in an electronic or optoelectronic component, wherein said p-doped layer is in the electronic or optoelectronic component Based on an organic matrix material in the following layer structures: pin: with p-dopant p-doped semiconductor - intrinsically semiconductive layer - n-doped semiconductor; n-i-p: n-doped semiconductor - intrinsically semiconductive layer - p-doped semiconductor; or p-n or n-p transitions.
  • the conductivity of charge transport layers in the case of use according to the invention is substantially increased and / or the transfer of the charge carriers between the contacts and the organic layer is substantially improved in applications as an electronic component.
  • CT complexes are formed in a doped layer according to the invention when the quinoid bisimidazoles are used, in particular by the transfer of at least one electron from the respective surrounding matrix material to the dopant.
  • cations of the matrix material are formed, which are movable on the matrix material. In this way, the matrix material acquires a conductivity that is increased compared to the conductivity of the undoped matrix material.
  • Conductivities of undoped matrix materials are generally ⁇ 10 -8 S / cm, in particular frequently ⁇ 10 -10 S / cm. It is important to ensure that the matrix materials have a sufficiently high purity. Such purities can be achieved by conventional methods, for example gradient sublimation. By doping, the conductivity of such matrix materials can be increased to greater than 10 -8 S / cm, often> 10 -5 S / cm. This applies in particular to matrix materials which have an oxidation potential greater than -0.5 V vs. Fc / Fc + , preferably greater than 0 V vs. Fc / Fc + , in particular greater +0.2 V vs. Fc / Fc + exhibit.
  • the term Fc / Fc + refers to the redox pair ferrocene / ferrocenium, which is used as a reference in an electrochemical determination of potential, for example cyclic voltammetry.
  • the dopants described in this invention have a surprisingly high stability with respect to their reactivity with the atmosphere.
  • the bisimidazoles used as dopants in addition to the depicted quinoid form, also have pronounced biradical character or zwitterionic character in their most stable structure ( A. Kikuchi, H. Ito, J. Abe, J. Phys. Chem. B 2005, 109, 19448-19453 ; A. Kikuchi, F. Iwahori, J. Abe, J. Am. Chem. Soc. 2004, 126, 6526-6527 ; T. Suzuki, et al., Tetrahedron Lett. 2003, 44, 7881-7884 ; K. Okada et al., Chem. Lett. 1998, 891-892 ; M. Kozaki, A. Isoyama, K.
  • the described quinoid bisimidazoles can be synthesized by known methods.
  • the preparation is based on the provision of benzoic bisimidazoles, which are converted into their anions and converted by suitable oxidants into the quinoid bisimidazoles, according to the following general scheme:
  • R any branched or unbranched alkyl radical or substituted alkyl radical.
  • X aryl or heteroaryl
  • the quinoid bisimidazoles used as p-dopant can also be produced by photochemical excitation of suitable precursors, for example under UV irradiation ( Y. Sakaino, J. Org. Chem. 1979, 44, 1241-1244 ). These precursors are usually alkoxy adducts of the quinoid bisimidazoles, which in turn are accessible by the addition of alcohols in the base-catalyzed oxidation of benzoiden bisimidazoles to quinoid bisimidazoles.
  • the tetrabromobisimidazole B was prepared by bromination of commercial bisimidazole A as a modification of a known procedure ( K. Lehmstaedt, H. Rolker, Ber. Dt. Chem. Ges. B 1943, 879-891 520 mg (3.88 mmol) of bisimidazole and 2.13 g (15.7 mmol) of sodium acetate trihydrate are initially charged in 10 mL of glacial acetic acid, and a solution of 2.48 g (15.5 mmol) of bromine in 10 mL of glacial acetic acid is added dropwise , After complete addition, the mixture is heated to 100 ° C for 2 h.
  • the representation of the quinoid dopant C was carried out in a modification of a known regulation ( S. Dedik et al. Khimiya Gel. Soed. 1989, 10, 1421 by heating 565 mg (1.26 mmol) of tetrabromodiimidazole B with 428 mg (2.52 mmol) of silver nitrate in 40 ml of absolute EtOH for 1 h at reflux and suctioning off the product formed. This product was suspended in 20 mL of absolute dichloromethane, cooled to 0 ° C and treated with 12.8 mL of 0.1 M bromine in dichloromethane.
  • phthalocyanine complexes for example, Zn (ZnPc), Cu (CuPc), Ni (NiPc) or other metals, wherein the Phthalocyaninligand may also be substituted, can be used.
  • Other metal complexes of naphthocyanines and porphyrins may optionally be used.
  • arylated or heteroarylated amines or benzidine derivatives which may be substituted or unsubstituted, for example TPD, ⁇ -NPD, TDATA, in particular spiro-linked arylamines such as spiro-TTB, may also be used as the matrix material.
  • ⁇ -NPD and spiro-TTB can be used as the matrix material.
  • heteroaromatics such as, in particular, imidazole derivatives, thiophene, thiazole derivatives, heterotriphenylenes, but also others can be used as the matrix material, if appropriate also dimeric, oligomeric or polymeric heteroaromatics.
  • the heteroaromatics are preferably substituted, in particular aryl-substituted, for example phenyl or naphthyl-substituted. They can also be present as spiro compounds.
  • matrix materials mentioned can also be used with one another or mixed with other materials in the context of the invention. It is understood that suitable other organic matrix materials having semiconducting properties may also be used.
  • the p-dopant is preferably present in a doping concentration of ⁇ 1: 1 relative to the matrix molecule or the monomeric unit of a polymeric matrix molecule, preferably in a doping concentration of 1: 2 or less, particularly preferably 1: 5 or less or 1:10 or smaller.
  • the doping concentration may be in the range of 1: 1 to 1: 100,000, especially in the range of 1: 5 to 10,000 or 1:10 to 1,000, for example, in the range of 1:10 to 1: 100 or 1:25 to 1:50, without being limited thereto.
  • the electron-deficient quinoid bisimidazoles used according to the invention it is possible to produce semiconductive layers which may be more linear in shape, e.g. as conductivity paths, contacts or the like.
  • the quinoid bisimidazoles can be used here as p-dopants together with another compound which can function as matrix material, wherein the doping ratio can be 1: 1 or less.
  • the p-dopant used may also be present in higher proportions to the other compound or component, so that the ratio of dopant: compound can be in the ratio> 1: 1, for example in the ratio ⁇ 2: 1, ⁇ 5: 1, ⁇ 10: 1 or ⁇ 20: 1 or higher.
  • the respective other component may be one which can be used as matrix material trap for the production of p-doped layers, without being limited thereto.
  • the region containing a p-dopant can in particular be electrically conductively contacted with an organic semiconductive material and / or an inorganic semiconducting material, for example, be arranged on such a substrate.
  • said electron-deficient quinoid bisimidazoles are used according to the invention as p-dopants, for example in a ratio ⁇ 1: 1 or ⁇ 1: 2.
  • p-dopants for example when using ZnPc, spiro-TTB or ⁇ -NPD can be achieved as matrix semiconducting layers with conductivities at room temperature in the range of 10 -5 S / cm or higher.
  • ZnPc phthalocyanine-zinc
  • a conductivity of higher 10 -5 S / cm was achieved in the embodiment.
  • the conductivity of undoped phthalocyanine zinc is a maximum of 10 -10 S / cm.
  • the p-dopant layer or structure may each contain one or more different such electron-deficient quinoid bisimidazoles.
  • the term "electronic components” also includes optoelectronic components.
  • the electronic properties of an electronically functionally effective region of the component such as its electrical conductivity, light-emitting properties or the like, can advantageously be changed.
  • the conductivity of the p-doped layers can be improved and / or the improvement of the charge carrier injection of contacts into the doped layer can be achieved.
  • the invention comprises organic light-emitting diodes (OLEDs), organic solar cells, field-effect transistors, organic diodes, in particular those with a high rectification ratio such as 10 3 -10 7 , preferably 10 4 -10 7 or 10 5 -10 7 , and organic field-effect transistors by means of the electron-poor quinoid bisimdazoles as p-dopant can be.
  • OLEDs organic light-emitting diodes
  • organic solar cells in particular those with a high rectification ratio such as 10 3 -10 7 , preferably 10 4 -10 7 or 10 5 -10 7
  • organic field-effect transistors by means of the electron-poor quinoid bisimdazoles as p-dopant can be.
  • the contact materials are here hole injecting, wherein on the p-side, for example, a layer or a contact of ITO or Au may be provided, or electron-injecting, n-side, a layer or a contact of ITO, Al or Ag can be provided.
  • the i-layer may also be omitted, whereby layer sequences with pn or np junctions can be obtained.
  • the use of the compounds described is not limited to the abovementioned embodiments, since the layer structures are supplemented or modified by introducing additional suitable layers.
  • OLEDs with such layer sequences in particular with p-i-n or with an inverse thereto, can be constructed with the compounds described.
  • organic diodes of the type of metal-intrinsic semiconductor-p-doped semiconductor (min) or optionally of the pin type, for example based on phthalocyanine zinc. These diodes show a rectification ratio (rectification ratio with respect to the current flow in the passage direction compared to the current flow in the reverse direction of the component) of 10 5 and higher.
  • p-dopants using the p-dopants according to the invention, electronic components having pn junctions can be produced, with the same semiconductor material being used for the p-doped and n-doped sides (homo-pn junction), and wherein the p-doped semiconductor material a described electron-deficient quinoid bisimidazole is used.
  • An electron-deficient quinoid bisimidazole is provided as the p-dopant, purified by at least one-time gradient sublimation in a high vacuum.
  • the submitted p-dopant is evaporated simultaneously with the matrix material.
  • the matrix material is phthalocyanine zinc or spiro-TTB, respectively.
  • the p-type dopant and the matrix material can be evaporated in such a way that the layer deposited on a substrate in a vacuum evaporation plant has a molar doping ratio of p-dopant to matrix material of 1:10.
  • Each doped with the p-dopant layer of the organic semiconductor material is applied to an ITO layer (indium tin oxide), which is arranged on a glass substrate.
  • ITO layer indium tin oxide
  • a metal cathode is deposited, for example, by vapor deposition of a suitable metal to produce an organic light emitting diode.
  • the organic light-emitting diode can also have a so-called inverted layer structure, wherein the layer sequence is: glass substrate - metal cathode - p-doped organic layer - transparent conductive cover layer (for example ITO). It is understood that depending on the application, further layers can be provided between the individual layers mentioned.
  • the quinoid bisimidazole derivative C was used for doping ZnPc and spiro-TTB as a matrix material.
  • Doped layers with a doping ratio of dopant: matrix material of 1:10 were prepared by mixed evaporation of matrix and dopant.
  • the measured conductivities were 7.9x10 -5 S / cm in ZnPc and 4.6x10 -7 S / cm in spiro-TTB.

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EP07009366.1A 2007-05-10 2007-05-10 Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials Active EP1990847B1 (de)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP07009366.1A EP1990847B1 (de) 2007-05-10 2007-05-10 Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials
TW97117323A TWI471403B (zh) 2007-05-10 2008-05-09 咪唑衍生物及其使用作為摻雜有機半導體基材之摻雜物
PCT/EP2008/003792 WO2008138580A1 (de) 2007-05-10 2008-05-09 Imidazolderivate und deren verwendung als dotand zur dotierung eines organischen halbleitenden matrixmaterials
US12/599,487 US8460581B2 (en) 2007-05-10 2008-05-09 Imidazole derivatives and their use of dopants for doping organic semiconductor matrix material
JP2010506863A JP2010530845A (ja) 2007-05-10 2008-05-09 イミダゾール誘導体、および、イミダゾール誘導体の、有機半導体マトリクス材をドープするためのドーパントとしての使用

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EP07009366.1A EP1990847B1 (de) 2007-05-10 2007-05-10 Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials

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EP1990847B1 true EP1990847B1 (de) 2018-06-20

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US (1) US8460581B2 (enrdf_load_stackoverflow)
EP (1) EP1990847B1 (enrdf_load_stackoverflow)
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TW (1) TWI471403B (enrdf_load_stackoverflow)
WO (1) WO2008138580A1 (enrdf_load_stackoverflow)

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